


Owe You One

by justanotherbusyfangirl



Category: Supernatural
Genre: Blow Jobs, Crossdressing, Fake/Pretend Relationship, M/M, Oral Sex
Language: English
Status: Completed
Published: 2018-10-11
Updated: 2018-10-11
Packaged: 2019-09-12 03:53:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,014
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16865650
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: Castiel helps Dean escape crazy-eyes Becky at a work party.  Dean thanks him in a very personal way.





	Owe You One

“Holy shit,” Dean breathed, frozen in his doorway.  His eyes roamed Castiel up and down, taking in the unfamiliar appearance in front of him.  “Cas?” Dean asked, making sure he was looking at his friend, not some random, dark-haired girl who just happened to knock on his door.

The grin that answered was  _definitely_  Castiel’s grin, a gummy one with a scrunched up nose, that Dean had known for years.  Everything else, though, (except for the bright blue eyes that Dean also knew quite well), was unfamiliar.

Castiel was wearing black kitten heels, ones that didn’t look terribly uncomfortable or strange on a larger size foot than most dainty heels would.  His legs were shaved and shapely, but that was probably from how often Castiel went on runs.  (And Dean had a tingling memory from high school when Castiel was on the swim team – he’d definitely shaved his legs before this.  But still, that didn’t mean Dean was prepared to see his friend’s attractive, almost feminine legs.)

Because he could see Castiel’s legs, all the way up past the knee where his red skirt ended.  The skirt was the perfect split between tight and loose – just right so that it wouldn’t pull or reveal anything unfeminine while still being on the verge of sexy.

Castiel was wearing a flowy, silk tank top that was tucked into his skirt, with a sweater over it.  The sweater was three-quarter sleeve, though, and Dean noticed that the hair on Castiel’s arms had been removed too.   _Damn, he’s really into this_ , Dean thought to himself.

Dean’s eyes kept moving, his mind choosing to ignore the million questions about  _How the hell did Cas have boobs right now?_  and choosing to admire the familiar – yet unfamiliar – face before him.  

Castiel’s makeup was light, but attractive.  He had accentuated all of the feminine features on his face while covering up the masculine ones.  His blue eyes popped, as did his cheekbones.  He was wearing a wig, but had the hair pulled half back so that only some rested against his shoulders.  A few bangs fell onto his forehead, framing his forehead and cheeks nicely.

“Well, are you going to let a girl inside, or just leave me stranded out here in your hallway?” Castiel asked, putting a hand on his hip.  Dean laughed, unable to stop himself.

The way Castiel was standing, he looked like the perfect picture of an annoyed girlfriend.

And Dean supposed that was the point.

“Nah, we need to go anyway.  Gonna be late,” Dean said, turning to grab his keys from the table by the front door and locking his apartment, ushering Castiel to the elevator.  It was a natural movement for Dean to put his hand on the small of Castiel’s back to guide him, but at the same time Dean felt incredibly self-conscious at the act.

Castiel was quiet in the elevator as Dean kept staring.  Finally, he broke the silence.  “Told you I was good at it,” he said, making Dean look at him properly.  Dean nodded, an impressed look on his face.

“Dude, you could pass for a girl, it’s incredible,” Dean said, hoping Castiel would take it as a compliment.  “And I owe you big time for this, you’re the best.”

Castiel smiled, following Dean out of the elevator and to the Impala.  “If I couldn’t pass for a girl, I wouldn’t have claimed I could, Dean,” Castiel said as they got in the car.  Once they were sitting and Dean was turning the key in the ignition, Castiel continued.  “And you do owe me big time.  Especially if anyone figures out it’s me.”

Dean grinned at Castiel.  “Don’t worry, sweetheart,” Dean said, turning on the charm Castiel had seen him use on girls for years.  Dean’s hand went to Castiel’s knee, making Castiel’s stomach flip a bit.  “Nobody will know it’s you but me.”

With an obnoxious wink, Dean backed out of his parking place and headed out onto the street toward his office.  They were going to a work event and Castiel was acting as Dean’s girlfriend. 

Because of course, he’d been an idiot and claimed he had a girlfriend to fend off a girl in the office who had crazy eyes.  She’d insisted that Dean bring his ‘girlfriend’ to the party, and Castiel had stepped up to offer his help.

Castiel was the bestest best friend Dean could hope for.

They were obviously not the first ones to arrive, as the parking lot at the office was fairly full.  They got out of the car and met at the hood, giving each other a final once-over.  “So, uh,” Dean said, obviously getting nervous.  “We still good?”

Castiel smiled and batted his eyelashes, making Dean laugh some of his nerves away.  “Yeah, I’m good,” Castiel replied, his voice a bit higher than normal.  Upon Dean’s side-eye, Castiel shrugged.  “Gotta have a girlier voice than normal, right?”

Dean shrugged, realizing Castiel was right.  “So, what should I call you?” Dean asked.  “My friends at work have heard about you, Castiel, so I can’t say that’s your name…”

Castiel thought for a minute, before answering simply, “Cassie.  It’ll be close enough to Cas, which you call me all the time anyway, so you shouldn’t have terrible slip ups.”

Dean nodded, turning to the building.  “You’re the best, seriously,” Dean said, offering his arm.  Castiel took it, holding it the way a girl would.

And just like that, they were heading inside.

Truth be told, the party went a million times better than Dean would have ever imagined.  Castiel was a hit, acting the perfect girlfriend the entire time.  He charmed Dean’s superiors while keeping Dean company.

He even got crazy-eyes Becky off Dean’s back.  She was obviously shocked at the fact that Dean had actually brought someone with him to the party, and then mysteriously vanished after Castiel had gone ‘to the ladies’ room.’

Dean pulled him aside for that comment.  “Dude, you went to the bathroom – the  _girl’s_  bathroom?”

Castiel laughed.  “Of course, Dean.  I had to pee, where was I supposed to go, the men’s?  Besides, it’s all stalls in there.  No big deal.”

Dean gave him a look.

“So, Becky was in the bathroom too,” Castiel admitted.  “She tried to give me a talking to, saying you were a pig and always flirted with her.  She told me to break up with you, for my own good.”

Dean’s eyes grew wide.  He couldn’t believe Becky would lie like that.

Castiel shrugged.  “I just gave her a few…graphic things to think about that you do to me every night, and that jealousy wasn’t a good color on her.”

Dean choked.

Castiel just laughed, obviously thinking he’d impressed Dean and Dean had just swallowed the wrong way, but that wasn’t quite what was going on.

All of a sudden, Dean’s mind was down in the gutter, imagining all of the so-called graphic things that he and Castiel could get up to, especially with the way Castiel looked tonight.  Dean hadn’t ever thought of his friend that way, but now that the idea was in his head, he couldn’t stop thinking about it.

He shook his head, looking anywhere in the room but Castiel.  Luckily, the party was beginning to die down, many of his coworkers leaving.  He was dragged into a few short goodbye conversations before Castiel’s hand found his elbow.

“You wanna leave?” Castiel asked him, not sounding like he cared one way or another.  Dean looked over at him.

All Dean could think of when he looked at him was the two of them in very compromising positions.

Dean nodded, tongue stuck in his throat.  Castiel led him toward the door, stopping by Dean’s boss for a goodbye to him and his wife.  Dean only smiled, not trusting his voice.

The car ride home was quiet.  Dean couldn’t tell if it was an awkward quiet or normal one, since his skin was overheated and his mind was elsewhere.  Castiel didn’t seem to mind, though.

They headed up to Dean’s apartment, a promised drink waiting to pay Castiel for the evening.  Dean went to the kitchen to grab a couple beers, popping the tops off on the edge of his counter.  When he walked into his living room, Castiel was taking his wig off, his fake boobs laying on the coffee table.

Dean froze, the sight of his friend in the outfit hitting him again.

Castiel looked  _good_.

“See something you like, Dean?” Castiel asked cheekily, making Dean swallow.  He didn’t answer, walking over to hand Castiel his beer instead.

Castiel eyed him, knowing that Dean’s silence meant something.  He also knew that Dean would say that something when he was ready, so Castiel chose to sit and wait.

Dean chugged his beer, his mind rolling words over in his head to find the right thing to say.  When he put the empty bottle on the coffee table (next to Castiel’s wig and fake boobs), he finally knew.

“I seriously owe you one, Cas,” Dean said.  Instead of sitting on the couch next to his friend, he kneeled in front of him, hands landing on Castiel’s knees.  Castiel sat up a little straighter but didn’t flinch away, a good sign, Dean thought.  “Can I, uh, show you how much I appreciate you?”

One of Dean’s hands slid up Castiel’s smooth leg until he was toying with the bottom of Castiel’s skirt.  Castiel’s eyes followed the movement and he swallowed.

Dean watched the resolve in Castiel’s eyes as he took a drink of his beer and put it aside, sliding down on the couch a bit.  The movement hiked the skirt up a little and made Castiel’s legs spread around Dean’s body just slightly.

Castiel nodded to Dean.

Dean’s hands slid up and under Castiel’s skirt until they reached his (quite feminine) underwear line.  He kept hold of Castiel’s eyes as he slid the underwear and off down Castiel’s legs before settling his body closer.  Dean bit his lip as one hand moved back up and under Castiel’s skirt, finding the throbbing erection beneath.

Thank God Castiel was enjoying this already, or Dean would have known he was in the wrong.

Before he could overthink anything else, Dean leaned forward and down, flipping the end of the skirt over his head and sliding Castiel’s cock in his mouth.  It was heavy and thick, but the unique taste of Castiel had Dean groaning.  He heard Castiel gasp, vaguely aware of his friend’s hands gripping the sofa on either side of where he sat.

Dean’s tongue twirled around the head of Castiel’s dick before he took as much of it in his mouth as he could, the head hitting the back of his throat.  He scrunched his eyes closed and swallowed, knowing how good that felt to him.  From the noises Castiel was making, he liked it too.

A new determination blossoming in his chest, Dean sucked, licked, and moaned around Castiel’s cock, trying to give him the best blowjob ever.  It was the least Dean could do for what Castiel had done for him tonight, and so what if Dean was hoping this wouldn’t be the last time?

The last time for what, the blowjob?  Or the last time Castiel dressed up for him?

Dean pushed the thoughts away and pushed Castiel to orgasm, swallowing every last drop of tangy come before letting Castiel slip from his mouth.  He took a moment to breathe before backing out of the cover of Castiel’s skirt.

Castiel’s bright blue eyes were locked on Dean when he was revealed, a satisfied look on his face.  “Dean,” Castiel started, making Dean nervous.  He sat back on his heels to wait for Castiel to finish his thought.

Castiel’s mouth opened and closed like a fish a few times before he muttered, “Screw it,” and leaned forward, grabbing Dean’s face and kissing him hard on the mouth.

 _Thank God_ , was the last thing Dean thought before his mind was overwhelmed with the sensations of everything Castiel.


End file.
